Acetic Acid → HCID 10492977, compound

HRID 4950

Reaction equation

HRID 4950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][CH:7]=1.Cl.[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C:15](=O)[CH2:14]2.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]([NH:11][CH2:10][CH2:9][NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:14]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 11008376N1-(3-chlorophenyl)ethane-1,2-diamine

Product 1

HCID 10492977HCID 10492977, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(3-chlorophenyl)-1,2-diaminoethane (1 g; 0,00586 moles) in 25 ml of anhydrous methanol kept under nitrogen atmosphere, 3-quinuclidinone hydrochloride (1.01 g, 0.0062? moles) is added. The pH is adjusted to pH 6 by addition of glacial acetic acid. Sodium cyanoborohydride (0.74 g; 0.0117 moles) is added in two portions. The reaction mixture is refluxed for 10 hours, cooled and then filtered. After evaporation to dryness the residue is taken up with water, basified with 20% sodium hydroxide solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate and, after filtration, evaporated to dryness. The residue is purified by silica gel flash-chromatography (methylene chloride--methanol--30% ammonium hydroxide, 150:50:5 as eluant) to give the desired product as a clear oil (0.06 g).

Workup

  1. temperatureThe reaction mixture is refluxed for 10 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customAfter evaporation to dryness the residue
  5. extractionextracted three times with ethyl acetate
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationafter filtration
  9. customevaporated to dryness
  10. customThe residue is purified by silica gel flash-chromatography (methylene chloride--methanol--30% ammonium hydroxide, 150:50:5 as eluant)

Sources & evidence

ORD record
ord-6155d4e4a76d41d69a88452893850b2d
Source dataset
uspto-grants-1993_09
Patent number
US05242929

Linked notes

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